Producing substances resembling caoutchouc.



No Drawing.

UNITED sTA'rEs PATENT or-Fioa HENRY srALAY' ARTHUPL HOLT AND GERHARD STEIMMIG, or" LUDWIGSHAFEN-ON- THE-MINE, GERMANY, assrsnons' T0 BADISCHE ANILIN & sons. FABRIK, or-

LUDWIGSHAEEN-ON-THE-RHINE, GERMANY, A CORPORATION.

of 1.3-butadiene and of other hydrocarbons j of the same homologous series, such for instance as isoprene, 1-methyl-L3-butadiene and 2.3-di'methyl-1.3-butadiene, can be considerably accelerated and the yield of c'aoutchouc considerably increased if the butadiene or other hydrocarbon be polymerized in the presence of small quantities, that is to say about 3% of an organic substance contain- .ing oxygen in a loosely combined state.

Under this term applicants wish to have un derstood organic substances such as peroxids, superoxids, ozonids and the like. The substance may be capable either of itself giving up oxygen or of. acting as a carrier of oxygen. As instances of such substances we mention oxidized caoutchouc' (either natural or synthetic, and either vulcanized or not), which can be prepared, for instance, 4

by treating caoutchouc with oxygen or ozone, also butadiene or a member of the same homologous series which has been treated with ozone or other suitable oxidizing agent, an oxidized but undecomposed terpene containing at least tencarbon atoms in the molecule, and further benzoyl superoxid, but our invention is not limited to the use of these substances. The products obtainable according to our invention are charac'. terized by being insoluble in benzene, and only swelling when placed therein, and they thus differ from the products obtained according to Heinenianns British Patent No. 14,041 A. D. 1910.

In this application we make no claim specifically to theproduction of substances resembling caoutchouc by polymerizing a hydrocarbon of the butadlene series in the presence of an oxidized hydro-carbon of the Specification of Letters Patent.

raonucma SUBSTANCES BESEMBLING cmorrrcnouc.

Patented Feb. 18, 1010.

Application 'filed August 22, 1912. Serial No. 716,442.

butadiene series,- since specific ,claims for this process are contalned in our divisional .application, Serial No. 791,938 filed September 26th, 1913 on which the Patent No. 1,189,110 has been granted;

It is found that the use of an organic substance soluble in the butadiene series and containing oxygen in a loosely combined state is an advantage for the reason that such soluble organic. ozonids and the like exert a better action since they are uniformly distributed through the butadiene hydrocarbon. The oxygen of the organic substance is evolved from the dissolved state; that is, in the most intimate distribution and most complete contact conceivable with the butadiene hydrocarbons and the result is the polymerizing is carried forward to a higher degree and a substance insoluble in benzene is obtained.

The following examples will serve to illustrate the nature of our invention, but the invention is not limited to these examples.

Ea'aample 1.

Add to isoprene two per cent. of its weight of old oxidized caoutchouc and polymerize by heating for a considerable time at 100 C.

Example 2.

Emamp le 5.

Mix 100 parts by weight of isoprene with from 2 to 3 parts by weight of the product obtainable by acting on a terpene hydrocarbon with ozone, and then polymerize by heating for a considerabletime at 100 C.

Example 1;.

Mix 100 parts by weight of 2.3 dimethyl- 1.3-butadiene With 3 parts by weight of 2.3-dimethyl-1.3-butadiene ozonid (obtainable from 2.3-dimethyl-LS-butadiene and ozone) and polymerize by heating at 100 C.

11m team In this example, instead of 2.3-dimethyl- 1.2-butadiene ozonid, isoprene ozonid may be employed.

1. The process of producing substances resembling caoutchouc and being insoluble in benzene by polymerizing a hydrocarbon of the butadiene series in the presence of about three er cent. of an organic substance taining oxygen in a loosely combined state.

2. The process of producing substances resembling caoutchouc and being insoluble in benzene by polymerizing a hydrocarbon of the butadiene series in the presence of about three per cent. of an oxidized but undecomposed terpene, containing at least ten carbon atoms in the molecule.

3. The process of producing substances resembling caoutchouc and being insoluble in benzene by polymerizing a hydrocarbon of the butadiene series in the presence of about three per cent. of an'organi'e substance consisting of an ozonid containing oxygen in a loosel combined state and active chemically, sai

intimately with the hydrocarbon and reaching every part of it. soluble in t e butadiene hydrocarbon" con- In testimony whereof we have hereunto set our hands in the presence of two subscribing wltnesses.

ARTHUR HOLT.

GERHARD STEIMMIG.

Witnssesz' f ERNns'r C. EHRH D JosnPH PEIFIER.

organic substance being soluble. .in said hydrocarbon and capable of mixing 

